Various copolymers of MA-TIN 1,
2-[2-hydroxy-3-tert-butyl-5-(O-[2-hydroxy-3-(2-methylpropenoyloxy)propyl]-2-carbonyloxyethyl)phenyl]benzotriazole, and MA-TZ
1, 2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4-(2-hydroxy-3-[2-methylpropenoyloxy])propoxyphenyl]-1,3,5-triazine,
with styrene, methyl methacrylate, and
methacrylic acid have been synthesized by radical polymerization.
Their absorption spectra in the long-wavelength UV region appear unchanged compared to those of the monomeric
UV absorbers, indicating the
stabilizer chromophore to remain unimpaired in the course of the
polymerization. Both the monomeric and
the polymeric stabilizers exhibit a strongly Stokes-shifted,
temperature-dependent, low-quantum-yield
fluorescence which arises from an intermediate species formed by
intramolecular proton transfer. The
intramolecular hydrogen bond which is essential for the photostability
of this type of UV absorbers thus is
still intact in the copolymers. Activation energies for the
radiationless deactivation process can be evaluated
from the temperature dependence of the proton-transferred fluorescence.
These energies lie between 4 and
5 kJ/mol for most of the benzotriazole and triazine stabilizers
investigated and show hardly any matrix
dependence. Fluorescence-decay measurements with crystalline
MA-TIN 1 at different temperatures reveal
a close correspondence of the temperature dependence between decay
times and relative quantum yields.
The radiationless process thence is concluded to originate from
the proton-transferred level S1‘. The
decay
time at room temperature is estimated at 70 ps, close to the value for
crystalline TIN P. The proton-transferred
fluorescence of MA-TIN 1, in contrast, exhibits a biexponential decay
profile.
In a molecular unit which is a donor-fulgimide-acceptor triade, the possibility of an intramolecular energy transfer from donor to acceptor depends upon the isomer configuration of the photochromic fulgimide. It is shown that a switching on and off of this intramolecular energy transfer is possible by photoinduced shifting of the fulgimide levels between a trap and an antitrap function.
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